Patent GB-461957-A (GB)
Title: Improvements in or relating to substitutes for fatty alcohols
IPC: D06M13/152
Filed: 1935-05-22
Abstract: Substitutes for fatty alcohols are prepared by perhydrogenating by heating with hydrogen under pressure in the presence of known hydrogenation catalysts, compounds of the general formula R.Ar.OH or R.CO.Ar.OH, where R signifies an alkyl or alkaryl residue containing at least 6 carbon atoms (other than a nuclear tertiary alkyl group) for example, n- or iso-hexyl, n- or iso-heptyl, n- or iso-octyl, n-nonyl, n- or iso-decyl, n-undecyl, n- or iso-dodecyl, n- or iso-tetradecyl, n- or iso-hexadecyl, or n-or iso-docosyl, said residue being unsubstituted or having as substituents other OH groups or ether groups, and where Ar is an aromatic residue, for example that of benzene, naphthalene, phenanthrene, anthracene, diphenyl, diphenylmethane, diphenylethane, or phenylnaphthylmethane, which may have as substituents other alkyl residues, for example methyl and ethyl, ether groups, and other OH groups.  The compounds of the above formul  may be prepared by condensing phenols with primary or secondary alcohols, for example pentylmethyl-carbinol, b -ethyl-butyl alcohol, methyl-iso-butyl-carbinol, oleyl alcohol, 1.10-dihydroxydecane, ricinoleyl alcohol, or mixtures thereof; with the corresponding olefines; with aliphatic olefinic products having at least 6 carbon atoms from wood carbonization, coal distillation, the cracking of petroleum and paraffins, benzine syntheses, the fractionation of tar distillates, the destructive distillation of tar oils; or with olefines obtainable from chlor-paraffins by splitting off hydrochloric acid.  In examples: (1), (2) 4-octyl phenol or 4-octyl-2-methylphenol is perhydrogenated in presence of nickel; (3) 4-dodecyl-2-methyl-phenol is perhydrogenated in presence of copper chromite; (4) a mixture of 4 - sec. - alkyl - 2 - methyl - phenols (alkyl=C8H17 to C14H29) is perhydrogenated in presence of nickel oxide.  Other perhydrogenated bodies specified are 4-iso-hexyl-2-methylcyclohexanol, 4 - iso - octyl - 2 - methyl - cyclohexanol, 1-iso-undecyl-decahydronaphthol-2, 4-iso-octadecyl-cyclohexanol, 4-iso-docosyl-2-methyl - cyclohexanol, 5 - dodecyl - 2 - hydroxyperhydrodiphenyl, 4-(a -amyl-hexyl)-2-methyl-cyclohexanol.  The OH group of the perhydrogenated bodies may be esterified, for example by acetic, lactic, butyric, lauric, myristic, palmitic, oleic, linoleic, ricinoleic, stearic, benzoic, phthalic or wax acids; or etherified to form methyl, ethyl, m- or iso-propyl, n- or iso-butyl, decyl, dodecyl, tetradecyl, hexadecyl, phenyl, or benzyl ethers; or the perhydrogenated bodies may be treated with ethylene oxide, epichlorhydrin, or glycide; or they may be converted into halogenated (e.g. chlorinated or brominated) bodies.  The products may be used in the production of threads, for oiling artificial silk, in mercerizing, as assistants in the dressing, lubricating, spinning, spooling, dyeing, brightening, and finishing of textiles; for impregnating; for the production of superfatted soaps; as perfume fixing agents; in waxing, scouring, and polishing compositions, such as shoe creams and floor polishes; as wax substitutes, and as ingredients of pharmaceutical preparations.  Their derivatives, for example, their sulphonation products, may be used as disinfecting and vermin-destroying agents.  Specifications 254,753, 274,439, 320,638, [all in Class 2 (iii)], and 455,086 are referred to.  According to the Provisional Specification, the residue R contains at least 4 carbon atoms, and is further exemplified by n- and iso-butyl and n- and iso-amyl.  Perhydrogenated bodies specified include n-, sec-, tert-, and di-tert-butylcyclohexanol; methyl, ethyl, n- and iso-propyl, and cycloalkyl derivatives; and xanthic esters.